More buyers get confused by Harbour Square than any other building on this stretch of the Quay, and it's not really their fault. The name suggests one building. It's actually five, built across roughly two decades, sharing a name and a footprint but very little else.
The mistake I see constantly
A buyer finds a listing that says "Harbour Square," assumes it's a single, uniform building, and starts comparing its price per square foot against a completely different tower in the same complex. The comparison feels reasonable. It isn't. The five towers span from the original 1970s waterfront redevelopment through to the newest pair completed around 1990, and they don't share a condo corporation, a management history, or a reputation.
Why the confusion actually costs you
Fee structures, reserve fund health, and building condition all vary tower to tower within the complex. Assuming one tower's numbers apply to another can lead you to either overpay based on a rosier picture from a different building, or walk away from a genuinely good unit because you were comparing it against the wrong data.
How to actually navigate it
Always confirm the specific address, not just "Harbour Square," before you compare anything. 77 and 99 Harbour Square, known together as One York Quay, are the newest and most commonly transacted pair, roughly 39 to 40 storeys with distinctive blue-and-green window trim. The older three towers run smaller on average and carry their own separate fee structures and histories entirely.
What actually stays consistent across the complex
Some things genuinely are shared. The indoor saltwater pool, squash courts, the shuttle bus service to the Financial District, and the direct connection to the Westin Harbour Castle apply complex-wide, regardless of which specific tower you're in. It's worth asking which amenities are shared and which are tower-specific, since the answer isn't always intuitive.
If a Harbour Square listing has caught your eye, the very first thing worth confirming is which of the five towers it's actually in. Everything else about the comparison depends on getting that right first.